Britney Spears’ Top 10 Wildest Looks

Stop The Presses!

Tiffany LeeDecember 2, 2011

Can you believe it? Britney Spears turns 30 years old December 2! And what better way to celebrate the all-grown-up pop icon's big birthday than to look back at some of her wildest ensembles? From bare midriffs to barely-there lingerie, Britney has rocked some of the most memorable looks in pop music during her decades-spanning career.

Sure, there's some (okay, a lot) of poking fun going on here, but I genuinely love my Brit Brit. Femme Fatale is in all honesty one of my favorite albums of the year, and this is coming from an underground music devotee. In fact, over 14,000 photos of Britney were thoroughly sifted through by yours truly to find Britney's craziest, most iconic outfits. And so, without further ado, here are her top 10 fashion moments!

10. I distinctly remember watching a show that followed Britney Spears while she had a fitting for the 1999 MTV Video Music Awards. Her sheer, sequined cardigan with a furry collar was meant to be worn over a dress, but the young pop singer insisted she wear just the outer part. The top had to be altered to barely keep Britney's chest covered...and here you see the iffy result!

9. She may have been wearing little, but there was so much going on with Britney's red-carpet arrival outfit for the 2002 VMAs. The leather halter minidress with a high lace slit, matched with unfortunate lace-up heels, was already enough. But to add the crocheted arm warmers and biker/military/dominatrix hat was just too much for me. But then again, maybe I forget what was considered hot in 2002.

8. Getting back to her old form, Britney surprised the 2011 BillBoard Music Awards audience when she accompanied Rihanna for her performance of "S&M," with the two pop divas wearing matching bondage suits and handcuffs. The rabbit mask put Britney's outfit over the top, making her look less like a Playboy Bunny, and more like a scary Donnie Darko rabbit. The awkward pillow fight at the end of the performance didn't help, either.

7. Paris Hilton made it a "thing" to carry her tiny chihuahua everywhere she went, including photo shoots and red carpets. Britney Spears jumped on that bandwagon briefly, awkwardly carrying an even tinier pup with her as a red-carpet accessory at the 2004 Billboard Music Awards. Paired with the ultimate oddball accessory, then-husband Kevin Federline, Britney's strange company upstaged an otherwise cute look.

6. Who can forget Britney's "Like A Virgin" moment? Madonna made the sexy wedding dress an iconic moment when she rolled around suggestively onstage in it at the very first MTV Video Music Awards in 1984; Britney and Christina Aguilera revamped the look when they performed with Madonna at the 2003 VMAs. Male fantasies all over the world came true when the Britney-Madonna kiss happened during the controversial performance...but no one seems to remember that Madonna and Xtina kissed, too!

5. Britney Spears had a few rough years in her twenties, with her divorce from Kevin Federline, the proceeding child custody battles, rehab, and that head-shaving incident (not to mention the umbrella incident). Her performance at the 2007 MTV VMAs was supposed to mark her triumphant return, but instead her slovenly demeanor and incredibly unfortunate wardrobe choice only added to her mountains of bad press. She apparently was encouraged to wear a sequined corset to hide what used to be her signature killer torso, but in the end she refused, opting for a more revealing bra-and-panty set...and more flesh than the audience was prepared for.

4. The uproar over this outfit seems silly nowadays, but for the then-squeaky-clean 18-year-old teen queen, her nude-tone bodysuit, made to look like she was wearing nothing but rhinestones and a thong, created a massive scandal. The singer opened with a short cover of the Rolling Stones' "(I Can't Get No) Satisfaction," then moved on to her huge single "Oops! I Did It Again." The innuendo of both songs was a bit too much for some parents to handle, but it marked the start of Britney's foray into becoming a grown-up pop diva.

3. I can't express how much I love Getty Images. This 11-year-old neon orange gem could've slipped under the radar, but I still dug it up! Part pimp, part musketeer, all hot mess, Britney Spears was a two-time winner at the 2000 Billboard Music Awards, but her outfit was a huge loss.

2. Justin Timberlake must be one of the most tolerant boyfriends ever for going along with this matching-denim disaster at the 2001 American Music Awards. If Britney wore her long denim dress alone, it would've been a minor red carpet miss...but the two together makes any onlooker ask, WHY?

1. This look made the top spot because it fulfilled all requirements for a wild outfit: it was skin-baring, sexy, sparkly, very daringly accessorized, and heck, girl looked drop-dead gorgeous! Britney Spears has had more fashion misses than most celebrities would feel comfortable with, but her harem outfit from the 2001 VMAs was so on-pop-point that famed wax museum Madame Tussauds immortalized the look with an extremely creepy wax figure. Forever frozen on a pole? I guess there could be worst shrines to Britney Spears.